This invention relates to ureas and isoureas and in particular their use as agricultural chemicals and particularly as herbicides.
U.S. Pat. No. 4,127,405 teaches compounds which are useful for controlling weeds in wheat having the formula ##STR1## wherein R.sub.1 is ##STR2## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA1 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA1 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy or 1-2 carbon atoms; PA1 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA1 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA1 W and Q are independently oxygen or sulfur; PA1 n is 0, 1 or 2; PA1 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA1 Y is methyl or methoxy; or their agriculturally suitable salts; provided that: PA1 R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 A' is H, Cl, Br, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, NO.sub.2 or CF.sub.3 ; PA1 A is ##STR10## where Q is O, S or ##STR11## T is O or ##STR12## where R.sup.III is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl when Q is O or S then PA1 R.sup.I is C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 alkyl substituted with 1-3Cl, F or Br, or one of CN or OCH.sub.3 ; C.sub.3 -C.sub.6 alkenyl substituted with 1-3Cl; C.sub.3 -C.sub.6 alkynyl substituted with Cl; C.sub.5 -C.sub.6 cycloalkyl; cyclohexenyl; cyclohexyl substituted with 1-3CH.sub.3 ; C.sub.4 -C.sub.7 cycloalkylalkyl or ##STR13## where R.sub.7 and R.sub.8 are independently H, Cl, CH.sub.3 or OCH.sub.3 ; PA1 n is 0 or 1; and PA1 R.sub.9 is H or CH.sub.3 ; when Q is O then R.sup.I is CH.sub.2 CH.sub.2 OR.sub.15 ; CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.15 ; ##STR14## where R.sub.15 is C.sub.2 H.sub.5, CH(CH.sub.3).sub.2, phenyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CCl.sub.3 ; ##STR15## where R.sub.16 is CH.sub.3, C.sub.2 H.sub.5, CH(CH.sub.3).sub.2, phenyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CCl.sub.3, and n' is 2 or 3; CH.sub.2 CN; ##STR16## where R.sub.6 ' is C.sub.1 -C.sub.4 alkyl; provided R.sup.I has a total of .ltoreq.13 carbon atoms; when Q is ##STR17## then R.sup.I is H; C.sub.1 -C.sub.6 alkyl; --CH.sub.2 CH.sub.2 OR.sub.10 ; --CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.10 ; where R.sub.10 is CH.sub.3, CH.sub.3 CH.sub.2, CH(CH.sub.3).sub.2, or phenyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3 -C.sub.6 cycloalkyl; C.sub.5 -C.sub.6 cycloalkenyl; C.sub.6 cycloalkyl substituted with any one of 1-2OCH.sub.3, 1-3CH.sub.3, --CH.sub.2 CH.sub.3 or CF.sub.3 ; C.sub.4 -C.sub.7 cycloalkylalkyl; --CH.sub.2 CN; --CH.sub.2 CH.sub.2 CN; ##STR18## where R' is H, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, F, Cl, Br, CN, NO.sub.2 or CF.sub.3 ; PA1 R" is H, CH.sub.3, Cl, F or Br; PA1 R.sub.7, R.sub.8 and R.sub.9 are as previously defined; PA1 R.sub.6 is H, C.sub.1 -C.sub.3 alkyl; CH.sub.2 CN; CH.sub.2 CH.sub.2 --CN or --CH.sub.2 --CH.dbd.CH.sub.2 and R.sub.6 and R.sup.I may be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 O--CH.sub.2 CH.sub.2 --; PA1 when A is ##STR19## then R.sup.II is H, C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 alkenyl; phenyl; benzyl; benzyl or phenyl substituted with 1-2Cl, 1-2OCH.sub.3, 1-2CH.sub.3 ; C.sub.5 -C.sub.6 cycloalkyl; C.sub.4 -C.sub.7 cycloalkylalkyl with the proviso that when T is .dbd.N--OR.sup.III, then R.sup.II must be C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl; PA1 B is ##STR20## where R.sub.4 is H or CH.sub.3 ; W is O or S; R.sub.5 is H, or CH.sub.3 ; with the proviso that either R.sub.4 or R.sub.5 must be H; PA1 R.sup.IV is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.4 alkenyl; PA1 R.sub.1 is ##STR21## where Z is N, CH or C--F; X=H, Cl, --CH.sub.3, --OCH.sub.3 or --OCH.sub.2 CH.sub.3 ; PA1 Y=H; Cl; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted with --OCH.sub.3, --OC.sub.2 H.sub.5, --CN, --CO.sub.2 CH.sub.3, --CO.sub.2 C.sub.2 H.sub.5, ##STR22## or 1-3 atoms of F, Cl, Br; C.sub.3 -C.sub.4 alkenyl; --O--(CH.sub.2).sub.n' O--(C.sub.1 -C.sub.3 alkyl) where a' is 2 or 3; ##STR23## where L is OH, --NH.sub.2, ##STR24## --NH(C.sub.1 -C.sub.4 alkyl), --N(C.sub.1 -C.sub.4 alkyl).sub.2 or C.sub.1 -C.sub.6 alkoxy; SCN; --N.sub.3 ; NR.sub.11 R.sub.12 where R.sub.11 is H or CH.sub.3 and R.sub.12 is H, --OCH.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.2 -C.sub.3 alkyl substituted with OCH.sub.3 or OC.sub.2 H.sub.5, C.sub.1 -C.sub.2 alkyl substituted with --CN, CO.sub.2 H, CO.sub.2 CH.sub.3 or CO.sub.2 C.sub.2 H.sub.5, and R.sub.11 and R.sub.12 can be taken together to form --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- or CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; --O--R.sub.9 where R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, C.sub.1 - C.sub.2 alkyl substituted with cyano, C.sub.3 -C.sub.4 alkenyl, --CH.sub.2 C.tbd.CR.sub.13, ##STR25## R.sub.13 is H, CH.sub.3 or CH.sub.2 Cl; SR.sub.14 ; where R.sub.14 is C.sub.1 -C.sub.4 alkyl, allyl, propargyl or C.sub.1 -C.sub.2 alkyl substituted with CN; with PA1 the proviso that when X and Y are both H, then R.sup.I and R.sup.II are less than 5 carbons; PA1 X.sub.1 =H, Cl, OCH.sub.3, OCH.sub.2 CH.sub.3 or CH.sub.3 ; PA1 Y.sub.1 =H, OCH.sub.3 or CH.sub.3 ; and PA1 X.sub.II =O or CH.sub.2 and further provided that when A contains greater than 5 carbon atoms, then Y must contain .ltoreq.4 carbon atoms, and their agriculturally suitable salts. PA1 Z is CH or N; PA1 X is CH.sub.3 or CH.sub.3 O; and PA1 Y is C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 ; OCH.sub.2 CH.sub.3, CN or 1-3 atoms of F, Cl or Br; ##STR31## where L is NH.sub.2, OH, ##STR32## N(CH.sub.3).sub.2, NHCH.sub.3, C.sub.1 -C.sub.2 alkoxy; SCN; N.sub.3 ; NR.sub.11 R.sub.12 where R.sub.11 is H or CH.sub.3 ; R.sub.12 is H, CH.sub.3, CH.sub.3 CH.sub.2, OCH.sub.3 ; OR.sub.9 where R.sub.9 is CH.sub.3, CH.sub.3 CH.sub.2 ; CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C.tbd.CH; R.sub.9 is also C.sub.2 alkyl substituted with 1-3F, Cl or Br; CH.sub.3 S; PA1 Z is CH or N; PA1 X is CH.sub.3 or CH.sub.3 O; and PA1 Y is C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 ; OCH.sub.2 CH.sub.3, CN or 1-3 atoms of F, Cl or Br; ##STR42## where L is NH.sub.2, OH, ##STR43## N(CH.sub.3).sub.2, NHCH.sub.3, C.sub.1 -C.sub.2 alkoxy; SCN; N.sub.3 ; NR.sub.11 R.sub.12 where R.sub.11 is H or CH.sub.3 ; R.sub.12 is H, CH.sub.3, CH.sub.3 CH.sub.2, OCH.sub.3 ; OR.sub.9 where R.sub.9 is CH.sub.3, CH.sub.3 CH.sub.2, CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 .tbd.CH; R.sub.9 is also C.sub.2 alkyl substituted with 1-3F, Cl or Br; CH.sub.3 S; PA1 M is a cation of an alkalii metal or of a tertiary amine of up to 12 carbon atoms; PA1 A', W', B, are as previously defined. PA1 W' is oxygen or sulfur; PA1 A' is H, Cl, Br, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, NO.sub.2 or CF.sub.3 ; PA1 R.sup.I is C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 alkenyl; C.sub.3 -C.sub.6 alkynyl; C.sub.2 -C.sub.6 alkyl substituted with Cl, CN or OCH.sub.3 ; C.sub.3 -C.sub.6 alkenyl substituted with 1-3 Cl; C.sub.3 -C.sub.6 alkynyl substituted with Cl; C.sub.5 -C.sub.6 cycloalkyl; cyclohexenyl; cyclohexyl substituted with 1-3 CH.sub.3 ; C.sub.4 -C.sub.7 cycloalkylalkyl or ##STR55## where R.sub.7 and R.sub.8 are independently H, Cl, CH.sub.3 or OCH.sub.3 ; PA1 n is0 or 1; and PA1 R.sub.9 is H or CH.sub.3 ; --CH.sub.2 CH.sub.2 OR.sub.15, CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.15, ##STR56## where R.sub.15 is C.sub.2 H.sub.5, CH(CH.sub.3).sub.2, phenyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CCl.sub.3 ; --CH.sub.2 CH.sub.2 O--.sub.n, R.sub.16, ##STR57## R.sub.16 where R.sub.16 is CH.sub.3, C.sub.2 H.sub.5, CH(CH.sub.3).sub.2, phenyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CCl.sub.3, and n' is 2 or 3; CH.sub.2 CN; ##STR58## where R.sub.6 ' is C.sub.1 -C.sub.4 alkyl; provided R.sup.I has a total of .ltoreq.13 carbon atoms. PA1 A', W' and CO.sub.2 R.sup.I are as defined previously for structures I", II" and III".
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA2 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA2 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA2 with the proviso that when R.sub.6 is CH.sub.2 CH.sub.2 CN or CH.sub.2 CN, then R.sup.I is CH.sub.2 CH.sub.2 CN or CH.sub.2 CN; and R.sup.I and R.sub.6 have a total carbon atom count of .ltoreq.13; and when R.sup.I is OCH.sub.3 or OCH.sub.2 CH.sub.3 then R.sub.6 is CH.sub.3 or H;
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR3## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al. Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR4## wherein R is butyl, phenyl or ##STR5## and R.sub.1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR7## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974), ##STR8## wherein R is pyridyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, barley, wheat, and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Prevention or minimizing the loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing, or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists, however, for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.